48 Hours in Sag Harbor, New York

An insider's guide to the best kept secret in The Hamptons, Sag Harbor

Words by Christine Breslin
May 29th, 2018

John Steinbeck and Paul Newman had it right when they retreated to the salt swept Long Island Sound. However, they weren’t the only ones to choose this tranquil spot. Fifty plus years later, nestled between the North Fork’s star-studded Bridgehampton and East Hampton, a small Victorian whaling village composed of free-and-easy locals, shingle-style architecture and inconceivable food is still the desired destination of the East End hamlets. With an amalgamation of the new and old, Sag Harbor is home to historic buildings, shelled beaches and deep-water marinas which host the largest Hampton yachts. Just an hour and a half outside of New York City, Sag Harbor is no longer the ‘Un-Hampton’ of the Hamptons but the holiday enclave of the summer season.

How to Get There

The Hampton Jitney and Ambassador are the easiest ways to get to Sag Harbor. With several pick-up and drop off locations around NYC and neighbouring boroughs, the Jitney will bring you to the epicentre of Sag Harbor, Main Street. You can buy single Jitney tickets online for €16 and from €34 for a plush seat on the Ambassador, you can watch movies and have wine onboard.

From Pennsylvania Station in NYC, you can get on board the Long Island Rail Road Service. The train disembarks in the Hampton towns of Amagansett, Bridge Hampton, East Hampton, South Hampton and Montauk. From here you can take the Hampton Hopper to your chosen destination.

If public transport isn’t your style, hiring a car to get you from the high rises of New York to the peaceful banks of Sag Harbor Bay is the only way to travel. Enterprise-Rent-A-Car offer rates of €68 per day and are available from all international airports and 44 locations throughout the five boroughs.

Where to Stay

The American Hotel

With 8 double rooms and a 75-foot yacht, The American Hotel is the most luxurious hotel you can inhibit whilst in the Hamptons. Each bedroom comes with a living area and all beds have Frette sheets and comforters to literally melt into. Built in 1846 at the height of the maritime industry, The American Hotel’s porch remains the ultimate spot for people watching whilst enjoying an aperitif. This hotel and restaurant will allow you to submerge yourself in the old school elegance of the town. Prices on application.

Baron’s Cove

During the forties and fifties, we all became aware of the creative figures that dominated the cafés in Saint Germain, Paris. However, Sag Harbor was an inlet for legends such as Truman Capote, John Steinbeck, Paul Newman and Art Garfunkel in the sixties. Their stomping ground was Baron’s Cove which sixty years later has been renovated with 67 harbour facing rooms. Baron’s Cove has harbourside heated saltwater pool, tennis court, fitness studio, spa services as well as complimentary beach service. With the best views of the harbour, it is not cheap at €453 a night but worth every penny.

Forever Bungalows

1.5 miles from the town centre, Forever Bungalows is a modern budget and eco-friendly retreat. With six detached bungalows and 8 hotel rooms, the Hamptons motel has accommodation from a Bungalow studio to a Hotel penthouse.


From cottages on Lily Pond to North Haven’s multi-bedroom escapes, Airbnb will offer all those frequenting Sag an authentic grasp of this wistful summer sanctuary.

How to Get Around


Ramble through the red-bricked Main Street or its end-to-end suburban streets via foot or rent a bike for €35-65 per day from Sag Harbor Cycle.


A gift from the heavens, Uber exists in Sag Harbor. Banished in East Hampton, Uber will cost €21 per journey but after a few cocktails, this service will trump the limited and expensive taxi services of the Hamptons.

Where to Eat, Drink and Be Merry

Estia’s Little Kitchen

Locally sourced and grown produce is the success behind Colin Ambrose’s restaurant. The Mexican inspired restaurant brought avocado toast and breakfast bowls to the forefront before they made any ‘Hamptonites’ must-have lists.

Golden Pear Café

Sag Harbor is not renowned for its brunch scene as most dwellers eat bagels by the pool or fruit salads from the local farmer’s markets in bed. However, the Golden Pear Café, situated in all Hampton towns, provides maple syrup strewn French toast, pancakes and porridge for those early risers.

Grindstone Coffee and Donuts

Grindstone makes 1,300 brioche doughed doughnuts every weekday and 2,000 each Saturday and Sunday. Four classic doughnuts grace the chalkboard’s regularly with four novel doughnuts popping up daily. After pilates and a turmeric iced tea, these thin mint and Nutella s’mores doughnuts will go down a treat.

Estia’s Little Kitchen
Grindstone Coffee and Donuts


Above the Sag Harbor Cove Yacht Club resides the casually-chic Beacon Restaurant. This no reservation hotspot draws celebrity crowds as well as a long wait, but the sunset views, endless cocktail menu and the crispy fish tacos will make you realise heaven is on earth.

Dopo la Spiaggia

Inspired by the Tuscan beaches, Dopo La Spiaggia is the upscale Italian restaurant that transcends oceans. With a small menu, this restaurant serves up basic dishes with an out of this world twist-think shaved brussel sprout salads, shitake ravioli and poached branzino. The executive chef, Maurizio Marfoglia, was previously behind Tutto Il Giorno.

Le Bilboquet

Overlooking the wharf, Le Bilboquet- formerly B. Smyths restaurant- has the best views of the water in Sag Harbor. Already established in NYC, Dallas and Atlanta, this French bistro is renowned for its Cajun Chicken. While you sip on cocktails on the terrace and absorb the intimate ambience don’t forget to take in the luxury yachts bobbing in front of you.

Le Bilboquet
Lulu’s Kitchen

Lulu’s Kitchen

Limos and chauffeur driven cars pull up outside this kitchen and bar throughout the summer season. With an open flamed kitchen, woodfired flatbread and signature cauliflower heads, this is the place to be for the 25 plus demographic.

Where to Shop


An oasis of tranquillity is the only way to describe Bloom. With panelled life-size hydrangea pots, shuttered windows and a picket fence outside, you enter what feels like the chic, nonchalant home of store owner Mona Nurenberg. Alongside art and casual ensembles, you will find the perfect gifts and textiles for every occasion.


Branded the most elegant interior store in the Hamptons, Monc XIII has an expertly selected range of new and vintage goods. From turmeric wellness tea to sixties Stilnovo ceiling lamps, Monc XIII will inspire you even if you don’t make a big purchase.

The Styliner by Joey Wöllfer

What started as the Styleliner Truck boutique in 2010, is now a treasure chest of luxe apparel, intricate jewellery and vibrant accessories on Madison Street in Sag Harbor. Joey Wöllfer, also co-owner of Wöllfer wine estate, hand picks her artisan-inspired collections both domestically and abroad each season.

What To Do This Season

Trawl Sag Harbor Farmers Market

From locally grown produce to organic infused olive oils, Sag Harbor Farmers Market on Bay Street plays host to a wide variety of East End exclusive products every Saturday between 9 am and 1 pm. We have a growing list of wants- and of course needs- this summer with new vendors being announced regularly.

Hit the Beach!

Sag Harbor has three must-visit beaches. Before hitting Sagg Main, Havens or Foster Memorial Beach, grab picnic essentials in Schiavoni’s Market or Cavaniola’s Gourmet. Sag Harbor Bay is remarkably calm and the ideal location for paddle boarding and sailing lessons. If staying in Baron’s Cove, they provide shuttles, chairs, umbrellas and towels for your beach excursions.

Travel Back in Time

Featured throughout the pages of Herman Melville’s classic Moby Dick, Sag Harbor has a historical story worth exploring. Sag Harbor’s preserved grounds and buildings such as the Umbrella House and Sag Harbor Whaling and Historical Museum pleasantly depicts the local history.

Wine and Dine at Wölffer Estate & Vineyard

Sag Harbor is home to new restaurant Wölffer Kitchen, the first winery-owned restaurant in the Hamptons. Once you have eaten the locally sourced food and tried the dry rose cider, you will want to further tour the vineyards, located 12 minutes outside of Sag Harbor.

Take the North Ferry to Shelter Island

Either by foot, bike or car, you can access Shelter Island via the North Ferry at the end of Sag Harbor’s well named Ferry Road. From €3-15 return journey, Shelter Island offers a wide variety of activities for everyone to enjoy. During the day, walk the Mashomack Nature Preserve which covers two-thirds of the island or get a guided Kayak tour of the five-mile Coecles Harbor Marine Water Trail. Have afternoon tea at the scenic Ram’s Head Inn and finish your day at Sunset Beach Hotel and Restaurant for some Hamptons glamour, a chilled glass of wine and fresh seafood dishes- the main ingredients are caught in the facing bay.

And Finally, Indulge…

In celebrity spotting.

Christie Brinkley, Billy Joel, Richard Gear, Jimmy Buffet and childhood favourite Julie Andrews are residents alongside designers Lisa Perry and Nicole Miller. Kourtney Kardashian, Jennifer Lopez, the Olsen’s, Steven Spielberg and many more have been pictured walking along Main Street.